Sr. AI Deployment Manager

About DialpadDialpad is the leading AI-powered customer communications platform, transforming how businesses communicate with their customers. More than 50,000 companies around the globe — including Netflix, RE/MAX, Uber, Randstad, and Tractor Supply — rely on Dialpad to build stronger customer connections using real-time, AI-driven insights.

Visit dialpad.com to learn more. Being a Dialer At Dialpad, you’ll be part of a collaborative team working toward our shared mission of making our customers and their employees wildly successful. We believe that every conversation matters, and we're elevating each one with a platform that drives real-time insights and automation for our customers.

We thrive on continuous evolution, where every employee leverages industry-leading AI to constantly refine our platform and our own skills. We seek individuals who not only meet our high standards but go beyond them. Our ambition is significant, and achieving it requires a team that operates at the highest level. We look for individuals who are not just ambitious but who also possess the traits that are fundamental to our success: Scrappy, Curious, Optimistic, Persistent, and Empathetic.

Your roleAs an AI Deployment Manager, you will lead the end-to-end delivery lifecycle of autonomous AI systems for our enterprise customers. Unlike traditional software, agentic AI involves non-deterministic logic and complex multi-step reasoning. You will lead a "Deployment Pod" consisting of Forward Deployed Engineers and AI Deployment Engineers to ensure our agents don't just "talk," but actually "do" work safely and effectively.

Your mission is to manage the RAID (Risks, Assumptions, Issues, Dependencies) of autonomous systems, ensuring that every deployment has clear guardrails, measurable KPIs, and high user adoption. Reporting to the Manager of Partner Professional Services, this is a hybrid role (3 days per week) based in our Kitchener office.

What You'll Do

Pod Leadership: Orchestrate a cross-functional team (FDEs, Architects, and Data Scientists) to deliver complex multi-agent systems. Scoping & Discovery: Work with customers to map their manual business processes (e.g., "Inbound Lead Qualification") into structured agentic "Skills" and "Tasks. " Risk & Guardrail Management: Lead the "Safety Review" of every deployment.

Ensure agents have clear limits on their authority (e.g., "The agent can draft an email but cannot hit 'Send' without human approval"). Evaluation & UAT: Define the "Gold Dataset" (the ground truth) for User Acceptance Testing. Manage the process of "grading" AI performance to ensure the agent meets the customer's accuracy requirements before go-live.

Integration Coordination: Oversee the mapping of agent tool-calling to connectors (CRM, ERP, Billing systems), ensuring security and data privacy standards are met. Change Management: Partner with customer business leads to help showcase the value of our Agents to increase adoption. Ensure Success: Define success criteria, capture appropriate data, and report out on successes and failures.  Skills you'll bring Experience: 5+ years in Technical Project Management, preferably in SaaS, CCaaS, or Enterprise AI.

AI Literacy: You understand the difference between a simple Chatbot and an Agent. You are comfortable discussing "Context Windows," "Hallucination Rates," and "Inference Costs. " Agile/Hybrid Mastery: Experience running sprints in a world where AI logic can be unpredictable. You know how to pivot when an agent's reasoning path fails during testing.

Stakeholder Management: The ability to explain to a non-technical customer why an AI made a specific "mistake" and how the team is adding a "control" to prevent it. Scrappy: You thrive in ambiguity, take full ownership of outcomes, and are driven by delivering tangible, measurable results for the customer, often working under tight timelines.

Culture Builder: You contribute to a dynamic team culture, focused on high-growth industry innovation, team collaboration, customer success, and having fun! Bonus Points Project management certifications (PMP, CAPM, PRINCE2, PMI-ACP). Telephony stack knowledge (WebRTC, SIP, SBCs). Experience deploying chatbots or voice bots at >10K daily conversations.

Contributions to open‑source AI agent frameworks. We believe in investing in our people. Dialpad offers competitive benefits and perks, alongside a robust training program that helps you reach your full potential. We have designed our offices to be inclusive, offering a vibrant environment to cultivate collaboration and connection.

Our exceptional culture, recognized repeatedly as a certified Great Place to Work, ensures every employee feels valued and empowered to contribute to our collective success. Don’t meet every single requirement? If you’re excited about this role and you possess the fundamental traits, the drive, and strong ambition we seek, but your experience doesn’t satisfy every qualification, we encourage you to apply.  Dialpad is an equal-opportunity employer.

We are dedicated to creating a community of inclusion and an environment free from discrimination or harassment.

Dialpad is where work comes together—one, beautiful workspace for anywhere communication & collaboration. Dialpad has built groundbreaking and truly unified products, including the industry’s most innovative business phone system, unlimited text and team messaging, one-click video meetings, and an AI contact center—all powered by the most advanced communications AI in the world.

Customers include WeWork, Uber, Motorola Solutions, Domo and Xero. Investors include Amasia, Andreessen Horowitz,...